diff --git a/examples/simple-game-server/Dockerfile.windows b/examples/simple-game-server/Dockerfile.windows
index b20770d6e4..7eddb67920 100644
--- a/examples/simple-game-server/Dockerfile.windows
+++ b/examples/simple-game-server/Dockerfile.windows
@@ -19,6 +19,7 @@
 
 # Build Stage
 ARG WINDOWS_VERSION=ltsc2019
+ARG IMAGE_TAG=""
 
 FROM --platform=linux/amd64 golang:1.21.6 as builder
 WORKDIR /go/src
@@ -29,7 +30,7 @@ WORKDIR /go/src/agones.dev/agones/examples/simple-game-server
 RUN GOOS=windows GOARCH=amd64 CGO_ENABLED=0 go build -o simple-game-server.exe main.go
 
 RUN ls -ltr /go/src/agones.dev/agones/examples/simple-game-server
-FROM mcr.microsoft.com/windows/servercore:${WINDOWS_VERSION}
+FROM mcr.microsoft.com/windows/servercore:${WINDOWS_VERSION}${IMAGE_TAG}
 
 WORKDIR /
 
diff --git a/examples/simple-game-server/Makefile b/examples/simple-game-server/Makefile
index 8004757813..d2d2bf1ac5 100644
--- a/examples/simple-game-server/Makefile
+++ b/examples/simple-game-server/Makefile
@@ -30,6 +30,10 @@ BUILDX_WINDOWS_BUILDER = windows-builder
 # For the full list of tags see https://hub.docker.com/_/microsoft-windows-servercore.
 # GKE-Windows version map: https://cloud.google.com/kubernetes-engine/docs/how-to/creating-a-cluster-windows#version_mapping
 WINDOWS_VERSIONS = ltsc2019 ltsc2022
+
+# https://github.com/microsoft/Windows-Containers/issues/493: Pin the LTSC2019 image to an older sha
+LTSC2019_IMAGE_TAG = "@sha256:6fdf140282a2f809dae9b13fe441635867f0a27c33a438771673b8da8f3348a4"
+
 WINDOWS_DOCKER_PUSH_ARGS = # When pushing set to --push.
 # Build with Windows support
 WITH_WINDOWS ?= 1
@@ -108,7 +112,7 @@ push-windows-image-%:
 build-windows-image-%: ensure-windows-buildx
 	cd $(root_path) && DOCKER_CLI_EXPERIMENTAL=enabled \
 		docker buildx build --platform windows/amd64 --builder $(BUILDX_WINDOWS_BUILDER) -f $(project_path)Dockerfile.windows \
-	 	--tag=$(server_tag)-windows_amd64-$* --build-arg WINDOWS_VERSION=$* . $(WINDOWS_DOCKER_PUSH_ARGS)
+	 	--tag=$(server_tag)-windows_amd64-$* --build-arg WINDOWS_VERSION=$* --build-arg IMAGE_TAG=$(if $(filter ltsc2019,$*),$(LTSC2019_IMAGE_TAG),) . $(WINDOWS_DOCKER_PUSH_ARGS)
 
 ensure-windows-buildx:
 # Windows image builds must be directed to a specific buildx context.
diff --git a/examples/xonotic/Dockerfile.windows b/examples/xonotic/Dockerfile.windows
index 991d232b0f..6d3024ecbe 100644
--- a/examples/xonotic/Dockerfile.windows
+++ b/examples/xonotic/Dockerfile.windows
@@ -35,6 +35,7 @@
 # See https://docs.microsoft.com/en-us/virtualization/windowscontainers/deploy-containers/version-compatibility
 # for details.
 ARG WINDOWS_VERSION=ltsc2019
+ARG IMAGE_TAG=""
 
 # Build Stage
 FROM --platform=linux/amd64 golang:1.21.6 as base
@@ -53,7 +54,7 @@ RUN curl -o xonotic.zip https://dl.xonotic.org/xonotic-0.8.6.zip && \
 
 
 # Final Image
-FROM mcr.microsoft.com/windows/servercore:${WINDOWS_VERSION}
+FROM mcr.microsoft.com/windows/servercore:${WINDOWS_VERSION}${IMAGE_TAG}
 
 WORKDIR C:/Xonotic
 
diff --git a/examples/xonotic/Makefile b/examples/xonotic/Makefile
index 01717cd0d5..d5eafda368 100644
--- a/examples/xonotic/Makefile
+++ b/examples/xonotic/Makefile
@@ -29,6 +29,9 @@ PROD_REPO ?= us-docker.pkg.dev/agones-images/examples
 WINDOWS_VERSIONS = ltsc2019 ltsc2022
 BUILDX_WINDOWS_BUILDER = windows-builder
 
+# https://github.com/microsoft/Windows-Containers/issues/493: Pin the LTSC2019 image to an older sha
+LTSC2019_IMAGE_TAG = "@sha256:6fdf140282a2f809dae9b13fe441635867f0a27c33a438771673b8da8f3348a4"
+
 # Build with Windows support
 WITH_WINDOWS ?= 1
 
@@ -86,7 +89,7 @@ push-windows-image-%:
 
 build-windows-image-%: ensure-windows-buildx
 	docker buildx build --platform windows/amd64 --builder $(BUILDX_WINDOWS_BUILDER) -f $(project_path)Dockerfile.windows \
-	--tag=$(server_tag)-windows_amd64-$* --build-arg WINDOWS_VERSION=$* . $(WINDOWS_DOCKER_PUSH_ARGS)
+	--tag=$(server_tag)-windows_amd64-$* --build-arg WINDOWS_VERSION=$* --build-arg IMAGE_TAG=$(if $(filter ltsc2019,$*),$(LTSC2019_IMAGE_TAG),) . $(WINDOWS_DOCKER_PUSH_ARGS)
 
 ensure-windows-buildx:
 # Windows image builds must be directed to a specific buildx context.